[Cl:1][C:2]1[C:13]2[CH2:12][CH2:11][CH2:10][C:9](=O)[C:8]3[CH:15]=[CH:16][CH:17]=[CH:18][C:7]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1.O.NN.[OH-].[K+]>C(O)CO>[Cl:1][C:2]1[C:13]2[CH2:12][CH2:11][CH2:10][CH2:9][C:8]3[CH:15]=[CH:16][CH:17]=[CH:18][C:7]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1The reaction of 9-chloro-5,6,7,8-tetrahydrodibenzo[a,c]cycloocten-5-one (3.0 g, 0.015 mole), 85% hydrazine hydrate (4.5 g, 0.076 mole), potassium hydroxide (3.0 g, 0.046 mole) and ethylene glycol (39 ml) produced an oil. The oil was purified by column chromatography on silica gel, eluted with toluene to yield 4-chloro-5,6,7,8-tetrahydrodibenzo[a,c]cyclooctene as an oil (3.3 grams).
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